Mel Ottenberg Picks His Favorite Oscars Looks of the Past 50 Years

There are no hard-and-fast rules to dressing for the Oscars, but history tells us that slaying the red carpet at the world’s most prestigious awards show is about daring to dream: to be minimal, to look incredibly stoned, to be almost naked, or to even drape oneself with a swan for the sake of the outfit. With the Academy Awards fast approaching, stylist and Interview Creative Director Mel Ottenberg got on the phone with Thom Bettridge to discuss some of his favorite Oscars red carpet looks of the last half-century—and the time he chipped his tooth on a Best Special Effects Oscar in a limo with Björk’s makeup artist.

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DIAHANN CARROLL, 1969

“Diahann is serious glamour. I have watched YouTube videos of this dress gliding across the stage a million times. It is so incredible, inspiring, daring, and cool. Diahann was crushing the red carpet before that was really a thing.”

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BARBRA STREISAND, 1969

“Barbra Streisand wearing Arnold Scaasi in 1969 is really hard to beat, because it’s absolutely everything. It’s that worst-dressed list outfit that’s actually the best thing ever. Babs claims she didn’t know it was see-through. Whether or not she knew, this look had maximum impact and was extraordinarily influential.”

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CHER, 1973

“I couldn’t give you one Cher outfit, so I’m giving you four that are all by Bob Mackie. This look from 1973 feels familiar now, because Kim [Kardashian] wore it as a Halloween costume and Naomi Smalls did it on Drag Race, but you know what, when your Oscar look from 45 years ago is a Halloween costume and a drag queen mainstay now, then you really nailed your 1973 Oscar look—didn’t you?”

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RAQUEL WELCH, 1979

“I have no idea what she’s wearing, but she looks so hot. Look at how hot she is. This is a look I truly love. People were dressing really sexy and cool in the late 70s at the Oscars—nobody really wants to look sexy or cool at the Oscars these days. That’s not a read, it’s just a fact.”

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CHER, 1984

“Look at how gangster Cher looks in this nude, beaded dress with fringe down the deep-V chest, and then this silk cape thing with the beading is killing me. Also, Cher with these insane long earrings is the 80s personified. And it’s very now—I would kill to put someone in this exact outfit right now.”

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CHER, 1986

“This is the most famous Cher outfit of all time. This is the Madame Tussaud’s freak-out outfit. This is daring and nasty. She knew exactly what she was doing, and in 100 years if the Earth is still here, people will still be talking about Cher’s 1986 Oscar look.”

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CHER, 1988

“Then in 1988, Cher comes back and gets that fucking Oscar. How old was she? Let me Google her DOB. 41! She’s 41 wearing this sheer dress with this cape, it’s so extraordinary. Goddamnit, Cher is so great. I think I might be Bob Mackie’s number one fan.”

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MARTHA PLIMPTON, 1989

“Martha in vintage with her slicked-back hair and arm-candy River Phoenix is the ultimate glamour for me. So chic. She absolutely stunned. Then River with no tie. It’s really about both of them. An incredible moment. Anything was possible.”

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KIM BASINGER, 1990

“Kim Basinger designed this asymmetrical ball gown disaster herself , and there was some sort of writing on the sleeve. So weird. I remember being 14 and watching this mess on TV. No, I did not like this. And, yes, I was turning my nose at it with the rest of the world. But, you know what? We’re still talking about it, and that’s what matters. I love this now, sure I do. Thank you, Kim!”

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MADONNA, 1991

“This Madonna moment is really top 3 Oscars outfits ever for me. She really did it. This is also Bob Mackie. She brought Michael Jackson, and she made it all about her. This is the most glamorous thing that ever happened. Period. Also, she didn’t even change into another look for her Best Performance, because the whole night was the ultimate performance! 10’s across the board for Madonna!”

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SUSAN SARANDON, 1996

“This chocolate explosion from Susan Sarandon—she just don’t give a fuck. Look at her glasses that are probably from the glovebox in her car. She’s probably totally blazed and that’s why she’s wearing glasses. I’m not totally sure, but I’m also totally here for it.”

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CLAIRE DANES, 1997

“This is Cerutti By Narciso Rodriguez, and Narciso is really nailing it! I love that you can see her foot. I love that she’s got a T-shirt tucked into a slip dress. Is that a satin bag? Everything about this is what I want for 2019. Claire is killing me in this little get-up.”

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SHARON STONE, 1998

“This is a look I talk about all the time. Sharon Stone in a Vera Wang skirt and her husband’s white Gap shirt is incredible. This shit is so fantastic. I’m sure she had an amazing stylist do it, but in my mind she just did this herself. I love Sharon and I think her husband was hot.”

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CELINE DION, 1999

“I remember the backwards white Dior suit like it was yesterday. This Dior Couture show had just happened, and fashion was gagged for this look. I remember Celine’s enthusiasm on the carpet, and I remember the crushing, cruel, decades-long backlash against Celine in this outfit. And where is she now? She’s just the most beloved queen of fashion is all. The universe came around for her. Celine was on the right side of history.”

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BJÖRK, 2001

“The Björk swan dress by Marjan Pejoski in 2001 is my number one favorite outfit I have seen in my entire life. I screamed out loud when I saw it. I guess I am still screaming. Yes, Björk! Talk about iconic. I met Björk that night at the Vanity Fair Oscar party. This was also the night that I chipped my tooth on the Best Special Effects Oscar for Gladiator in a limo on the way to an after-party at the Peninsula. That was probably the funnest night of my entire life.”

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RENÉE ZELLWEGER, 2001

“I can’t believe this is also 2001. This is vintage Jean Desses from Lily et Cie, and I remember Rita from the store telling me they did like 30 fittings. This is the dress that made Renée Zellweger an A-list actress. She looks so beautiful, so chic. It’s just fucking baller. A vintage look like this costs a lot of money. This is nobody’s freebie.”

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JULIA ROBERTS, 2001

“People were really nailing it in 2001. This is vintage Valentino. It’s not my favorite thing of all time, but it’s great. She’s a statue with a statue.”

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JENNIFER LAWRENCE, 2011

“J-Law in the red Calvin Klein kills. You didn’t know who J-Law was at this moment, and then she showed up in this thing looking so hot. It’s so simple, and since things are so structured and formal right now, I think some ingénue rocking a little thing like this could do really well to break through the noise. Minimal and killing it.”